Ross has said that when he first saw crack-cocaine as a teenager in 1979, he did not immediately believe it was a drug because it looked different from other drugs he had seen.[4]

The nickname Freeway came from Ross owning properties along the Los Angeles Harbor Freeway[5] and living next to the 110.[6] According to an October 2013 Esquire magazine article, "Between 1982 and 1989, federal prosecutors estimated, Ross bought and resold several metric tons of cocaine. In 1980 Ross' gross earnings were said to be in excess of $900 million – with a profit of nearly $300 million. Converted roughly to present-day dollars: 2.5 billion gross, and $850 million in profit, respectively.”[7] During the height of his drug dealing, Ross was said to have sold "$3 million in one day."[8] According to the Oakland Tribune, "In the course of his rise, prosecutors estimate that Ross exported several tons of cocaine to New York, Ohio, Pennsylvania and elsewhere, and made more than $600 million between 1983 and 1984."[9]

Ross began selling cocaine after failing to get a college sports scholarship to play tennis because of his illiteracy. He began spending time with an upholstery teacher at his school who revealed he dealt cocaine and offered Ross some to sell. Ross eventually began to ask for quantities to sell that exceeded what the teacher was willing to procure, so he turned to find a new dealer.[12]

Through a friend, Ross was introduced to a connection of two Nicaraguan exiles, Oscar Danilo Blandón and Norwin Meneses Cantarero, to purchase cheaper Nicaraguan cocaine. Ross began distributing cocaine at $10,000 less per kilo than the average street price, distributing it to the Bloods and Crips street gangs. Ross eventually purchased his cocaine directly from Blandón and Meneses instead of going through the connection. By 1982, Ross had received his moniker of "Freeway Ricky" and claimed to have sold up to US$3 million worth of cocaine per day, purchasing 455 kilos of cocaine a week.[8]

He initially invested most of his profits in houses and businesses, because he feared his mother would catch on to what he was doing if he started spending lavishly on himself. In a jailhouse interview with reporter Gary Webb, Ross said, "We were hiding our money from our mothers."[13]

With thousands of employees, Ross has said he operated drug sales not only in Los Angeles but in places across the country including St. Louis, New Orleans, Texas, Kansas City, Oklahoma, Indiana, Cincinnati, North Carolina, South Carolina, Baltimore, Cleveland, and Seattle. He has said that his most lucrative sales came from the Ohio area. He made similar claims in a 1996 PBS interview.[14] According to the Oakland Tribune, "In the course of his rise, prosecutors estimate that Ross exported several tons of cocaine to New York, Ohio, Pennsylvania and elsewhere, and made more than $600 million in the process."[9] Adjusting for inflation using the Consumer Price Index, this becomes more than a billion dollars.[15]

Much of his success at evading law enforcement was due to his ring's possession of police scanners and voice scramblers. Following one drug bust, an L.A. sheriff remarked that Ross's men had "better equipment than we have."[16]

According to the October 2013 Esquire article, “Between 1982 and 1989, federal prosecutors estimated, Ross bought and resold several metric tons of cocaine. In 1980 dollars, his gross earnings were said to be in excess of $900 million – with a profit of nearly $300 million. Converted roughly to present-day dollars: 2.5 billion gross, and $850 million in profit, respectively. As his distribution empire grew to include forty-two cities, the price he paid per kilo of powder cocaine dropped from as much as $60,000 to as low as $10,000. ” [6]

Ross's capture was facilitated by his main source, drug lord Oscar Danilo Blandón, who set up Ross. Blandón had close ties with the Contras, and had met with Contra leader Enrique Bermúdez on several occasions. Blandón was the link between the CIA and Contras during the Iran-Contra affair. Gary Webb interviewed Ross several times before breaking the story in 1996. Ross claims that the reason he was unfairly tried initially was because of his involvement in the scandal. Blandón received a 24-month sentence for his drug trafficking charges, and following his release, was hired by the Drug Enforcement Administration where he was salaried at US$42,000. The INS was ordered to grant Blandón a green card, despite the criminal convictions, to allow him to work for the DEA. The DEA has claimed they no longer employ Blandón, and his whereabouts are unknown.[17]

On June 18, 2010, Ross sued rapper Rick Ross (real name William Leonard Roberts II) for using his name,[18] filing a copyright infringement lawsuit against Ross in a California Federal Court.[18]Jay-Z had been called to testify in the lawsuit, as he was CEO of Def Jam when Ross was signed to the label.[18] Ross sought $10 million in compensation in the lawsuit.[18]

After the lawsuit was dismissed on July 3, 2010,[19] the album Teflon Don was released as scheduled on July 20, 2010. A federal judge ruled that the case should be refiled in California state court because it fell under California state law. Ross refiled the case with the State of California and the federal case is on appeal in the United States Court of Appeals for the Ninth Circuit.[20] The federal case was appealed to higher court, state case was filed in 2011 in California.

Freeway Ross has refiled in Los Angeles Superior Court with publicity rights claims. Depositions have been ongoing. Trial was set for early May 2012. The case was dismissed by a judge in the Los Angeles Superior Court.[21]

The California State case was updated with a motion in Freeway Rick Ross's favor as to Warner Brothers Records and their use of the name and image Rick Ross in July 2012.[22]

The New York Post reported that a trial was set for August 27, 2013 in Freeway Rick Ross versus Rick Ross and Warner Music Group.[23]

On December 30, 2013, the court ruled in favor of the rapper Rick Ross, allowing him to keep the name based on a First Amendment ruling.[24]

KCET TV wrote in a review, "(The book) is fascinating for its unsentimental, inside look at his career on the streets of South Central, which started for Ross with car theft and quickly shifted to drugs and the big time."[28] The autobiography was nominated for ForeWord Review's IndiFab Best Book of the Year Award 2014 for true crime.[29]

^"Dark Alliance: Library." San Jose Mercury News. April 9, 1997. Retrieved on December 14 2013. "A few years before, Ross became involved in cocaine sales, he was a player on his high school tennis team. A college scholarship was reneged once it was learned he couldn't read. The same day, he dropped out of high school his senior year weeks away from graduation.Photo from Dorsey High School yearbook"